


Inescapable Nightmare

by thursdayshunter



Category: Supernatural
Genre: Alpha Dean, Birth, Bottom Dean, Breeding, Breeding stand, Captivity, Castration, Come Inflation, Double Penetration in Two Holes, F/M, Face-Fucking, Forced Pregnancy, Forced Prostitution, Gags, Hurt Dean Winchester, M/M, Mpreg, Multi, Orgasm Denial, Other, Prostitute Dean, Restraints, Size Kink, Spitroasting, Surgery, Tentacle Monsters, Tentacle Rape, Tentacle Sex, Underage - Freeform, Unhappy Ending, Violent Sex, Voyeurism, mentioned Cas/OMCs, mentioned abaddon/cas/jimmy, mentioned alastair/cas/jimmy, mentioned jimmy/omcs, omegas castiel and jimmy
Language: English
Status: Completed
Published: 2017-01-03
Updated: 2017-01-03
Packaged: 2018-09-14 13:40:40
Rating: Not Rated
Warnings: Rape/Non-Con
Chapters: 1
Words: 4,296
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9183979
Author URL: https://archiveofourown.org/users/thursdayshunter/pseuds/thursdayshunter
Summary: Alastair was ruthless but Lucifer was more so and unfortunately it seemed that denying that alpha had only added fuel to an already volatile fire.“I’m afraid I was given very specific instructions on how to handle you, Winchester.” A cruel look overtook Alastair’s features.Prompt Fill





	

**Author's Note:**

> This was written for a prompt awhile back and I finally finished it off. Needless to say...READ THE TAGS!!!!!! You've been warned though if you've read my stuff before you know it's fucked up/kinky so you've got some idea at this point.
> 
> Once again I've written a prompt fill forwarded along to me. It's been awhile since I've written anything with tentacles...

Dean snarled in fury as he tried to twist out of his bindings but his arms remained tied firmly behind his back. “Untie me right fucking now, Alastair.” He knew his eyes were glowing alpha red but they had zero impact on the other alpha and his men.

He had been knocked unconscious and had woken up stripped naked with his arms tied behind his back. The sight of an ominous cave and the sound of the ocean lapping at the shore let him know they were very far from the city.

Fear threatened to choke him but Dean wasn’t going to give in. He wouldn’t go down to Alastair without a fight no matter how many alphas he was up against. There had been no way he was going to let the filthy alpha in front of him kidnap his little brother and on top of that give him to Lucifer of all alphas.

He’d heard about it and had sent Sam away to keep him safe. Dean hadn’t expected Alastair to make this kind of move against him but Dean should have known better.

Alastair was ruthless but Lucifer was more so and unfortunately it seemed that denying that alpha had only added fuel to an already volatile fire.

“I’m afraid I was given _very specific_ instructions on how to handle you, Winchester.” A cruel look overtook Alastair’s features, “ _If_ you survive this you’re going to spend the remainder of your days paying Lucifer back for the inconvenience you caused sending _Sammy_ away with your ass and mouth. He has very specific clients who enjoy fucking other alphas and a pretty one like you would be real popular at The Cage.”

Dean yanked at his bounds even harder, not liking the words or the look on the faces of the alphas surrounding him, as his eyes darted around trying to figure out why they were on some kind of island from the looks of it.

“You’ll spend days here, not long enough to starve of course, and if there is anything left then that’s the fate that awaits you. An alpha whore at The Cage.”

They hauled him into the cave where some kind of plant that clung to the walls and under the water seemed to cast an eerie blue light allowing him to see as they moved deeper.

“Though I doubt you’ll survive this.” Alastair’s laugh echoed in the cave, “I can’t see how an alpha could. They aren’t built for it after all.”

He fought harder but whatever they had given him while he was unconscious during the trip here made his movements sluggish. Dean snapped his teeth at an alpha trying to adjust their hold and moaned in pain when it earned him a hard blow to the face.

Dean’s vision swam as he was hauled along further and further until he could hear something up ahead.

“You should know before we leave that your precious baby brother Sammy was caught. The last time I saw him, right before we left with you, was completely naked, tied up and taking Lucifer’s dick in his slick little virgin omega hole.” The cruel words had Dean trying to shake off the dizziness and use his rage to lash out, “Lucifer had him gagged, caged and from the cherry red color of his ass spanked before he fucked right in.” lips curled in dark amusement, “No prep to loosen the way either.”

“You’re lying.” He denied because Sam _had_ to be safe. Dean had sent him out of the city to stay with Bobby and hopefully, eventually, to find a good alpha when he was old enough. Sam was far too young for the sick interest Lucifer had shown him.

There was no way Sam hadn’t made it to safety. But as he desperately thought that Alastair pulled out his phone, flicked through it and turned it for Dean to see.

His baby brother was completely tied up, gagged and getting fucked by none other than Lucifer himself. Sam’s ass was red from obvious hits, his back striped with what looked like a belt and when Alastair showed the picture with Sam’s face it was more than obvious Sam had been crying.

“I’ll kill all of you.” He hissed in fury as the phone was shoved into Alastair’s pocket and only earned him an amused laugh. The need to protect and seek revenge for the pain inflicted upon his far younger brother rising up in him in an uncontrollable wave of fury.

Then they were moving once more, the alphas ignoring him as he fought, and the sound of movement ahead was louder. His eyes widened in horror at the sight of the large creature. It was dark grey with white undersides and thick, long bulging tentacles that twisted and moved it around.

It couldn’t be an octopus because it had far too many tentacles for that. The creature below was something else, something otherworldly, that Dean thought belonged in a horror movie and not real life.

Around it he could see various bones, rocks and what he was sure was blood. Terror filled him and had him straining to get away from the alphas holding him. “Now, Dean, is that anyway to act towards the creature who is going to be keeping you company… _intimate_ for the next handful of days?”

The creature turned towards them as Dean was dragged towards the edge of the short little cliff. He tried leaning back but they easily shoved him over so he fell right into the deep pool of water below.

Dean struggled for air as he kicked to the surface as best he could and when he dragged in several gulps of air he immediately regretted it. The creature had sliced through the water towards him and thick tentacles curled around his bound form.

They hauled him through the water and back to the rocky, bone littered ground it had been on when he’d first seen it.

Above he could hear taunts and laughter as the creature used tentacles to spread his legs wide to the point of pain. Dean cried out at the stretch as his arms were crushed to his side, still tightly bound, and a slimy tentacle traced up his naked chest only to shove roughly down his throat when he gasped for breath.

His moans of pain and cries for help were cut off swiftly as the tentacle fucked down his throat causing him to gag, jerking in its tight hold, while another tentacle rubbed harshly against his hole.

Rubbed against his tight, dry and completely untouched hole.

Dean’s brain shorted out at the touch against his ass; a touch that he had never experienced and wasn’t physically equipped to take. The slimy appendage pushed against his hole, working its way inside of him, while the other continued to rapidly fuck down his throat.

The pain had him howling inside his mind, unable to vocalize it, as it pushed deeper and deeper inside without a care that Dean wasn’t made to be penetrated. Above him the leers and taunts rained down on him as the tentacle kept moving deeper.

It fucked up in short thrusts, trying to go further, as his hole was forced wide to accommodate the questing tentacle and it’s unnaturally impressive girth that only increased the further it pushed inside.

After what felt like hours the tentacle was buried far enough inside of him that the creature seemed satisfied. Immediately it started to roughly fuck up into him, pulling out and slamming back inside viciously, as Dean jerked and sobbed in its hold.

“How’s that feel, Winchester?” Alastair’s voice echoed in the cave, “I didn’t think it was possible for such a tight alpha hole to take something that large but your ass is spread open. If you survive this will be good training for when you’re getting your ass plowed by a never-ending line of alphas.”

More laughter reached his ears as both tentacles pounded into him unrelentingly at both ends.

“You can see it pressed up against your stomach. That thing filled up that virgin hole of yours completely. How deep is it?”

Tears ran unchecked down Dean’s cheeks as he struggled to breathe through the tentacle using his mouth and the pain pulsing through his body. His legs were spread even wider as it kept up the pace and Dean knew his ass had torn purely based on the amount of pain.

The entire time, even when the tentacle in his ass brushed his prostate causing small bursts of pleasure, his large alpha cock hung completely soft between his spread legs.

He wasn’t sure how long it used him but the alphas had disappeared long ago and soon the creature was shoving deep, pulsing and pulsing, before something even thicker pushed against his stretched rim.

Dean’s vision whited out at the pain as the hard thing pushed and pushed before it worked past the abused muscle. Whatever it was moved up inside of him, burning and hurting, before another was pushing against him.

Slowly his body seemed to get heavier, his stomach aching and his ass repeatedly stretched beyond anything he’d ever imagined, as the creature kept pushing up into him. Dean didn’t think an omega could survive this and he was struggling to maintain consciousness as whatever it was kept pushing up inside of him.

His wrists hurt violently from where they’d rubbed against his bindings, his shoulders pained him and everything ached. It was Hell on Earth and in the back of his mind he could only think that he’d failed his baby brother.

Finally the tentacle lodged inside of him moved back out only to be replaced by another. This time as it sunk deep, moving and twisting, it started to pulse rapidly as warmth flooded his insides.

It was only when the tentacle fucking his throat slipped out that Dean’s sobs and scratchy sounding pleads started to echo in the cave. “Please.” He managed, “Please stop.”

But the creature didn’t understand or it didn’t care. The pulsing continued and as Dean glanced down he could see a disgustingly obscene bulge where his flat belly had once been.

He felt a horrible pain as it dropped him on the ground, bound wrists crushed under the weight of his body, amongst the rocks and bones. Dean howled in agony as tears poured down his cheeks and his sobs echoed loudly in the cave.

The creature didn’t react and instead slipped into the water, disappearing from view, while Dean could only lay there with his bulging belly and excruciating pain causing his body to throb in agony. He could feel warm liquid sliding out of his gaping hole onto the cold ground and shivered at the sensation.

Dean’s eyes darted around trying to see if he could find the alphas who had left him there and saw nothing. The words from earlier came back to haunt him as he thought about being trapped here for days.

“Help. Please. Someone…help.”

His moans of pain were unanswered and any movement on his end only earned him white-hot pain racing through his abused body. Slowly unconsciousness dragged him under and it wasn’t until something was twisting inside of him, writhing and churning, that he was dragged back into the waking world.

A whimper escaped from his raw throat as he was turned onto his side by strong tentacles and one of his legs, tentacle curled around it, was bent and lifted. His insides hurt horribly as whatever it was going on inside of him moved and seemed to push down.

Dean’s mouth fell open as he panted and his body jerked in the creature’s hold as something forced its way out of his burning hole. “Stop. Please stop please please please please.” The words came out sobbed as yet another thing pushed out of his ass, spreading him wide and ripping, as the twisting and writhing inside of him continued.

It took four times of _something_ tearing its way from his ass that Dean realized they were smaller versions of the creature that had repeatedly raped him. Unspeakable horror filled him at the realization that the things that had pushed into him had been eggs or something and that his body had been used as a quick incubator.

But there was nothing he could do.

The creature kept his leg bent and lifted, keeping his ruined hole exposed, so its offspring could tear their way out of Dean’s abused body. Dean wasn’t sure how many he’d been fucked full of as each small creature forced its way from him until they slipped off one by one into the water, swimming away, before his leg was finally released.

A moan of pain slipped out as tentacles prodded at his gaping hole, leaking blood and something else, before the creature was hauling him up. Its thick tentacles found their way once more to fucking down his throat and shoving harshly up into his ass.

The process started over once more and Dean understood what Alastair had meant about _if_ he had survived being here for days.

Hours bled together as he was violently raped and once more the creature pushed its offspring up into Dean until his belly swelled obscenely. Then a new tentacle pushed into him, pulsing repeatedly, before slipping free.

Unconsciousness came quicker this time, Dean’s body simply unable to stay awake, while the creature’s offspring used his body to incubate.

Dean spent days drifting in and out of consciousness as the creature used him, bred him up and then held him in place while its offspring forced their way from his body only to disappear into the water.

It was after the most recent round of being raped and stuffed full of its offspring that Dean came around to the sound of voices. “Four hundred says he’s dead.”

“Six says that stubborn bastard is still alive.”

The voices got louder and louder as Dean moaned brokenly, body used and sore, as a loud whistle of appreciation sounded.

“Still alive.” It was Alastair, “But he sure looks on the verge of death, doesn’t he? I bet if we leave him a day or two more we’d come back to his bones licked clean.”

The laughter had Dean closing his eyes in defeat, unable to do anything but focus on the horrible pain and the way his body was full of the creature’s offspring. “We’ll wait till he’s whelped that creature’s offspring and then we’ll throw down the decoy before hauling him up.”

And that’s exactly what they did.

Dean could feel their eyes on him as he moaned and twisted while the small creatures inside of him writhed the closer they came to birth. Tentacles forced him into what Dean had come to know as the birthing position and then the alphas above watched as the creatures forced their way from his loose, ruined hole.

They slipped into the water, swimming off to who knows where, as Dean sobbed and cried out each time a new one pushed down to escape him.

“Awwww they took after their Mommy.” One of the alpha’s taunted, “I think that one had your eyes, Winchester. How does it feel to be a monster’s _bitch_?”

Above where he lay in agony, birthing the creature’s offspring, there were sobs and pleads from whoever they had brought as a decoy but Dean didn’t care. He wanted it to stop. He just wanted the pain to stop and as he passed out, hearing a splash and feeling the creature let him go, he hoped he died.

* * *

The sound of a machine beeping and the lethargic feeling weighing his limbs let Dean know he had not died. He shifted, groaning low, as the rattle of something caught his attention.

Dean blinked at the low light and turned his head to see a handcuff restraining his wrist to the side of the bed. A glance at the other side revealed another handcuff and shifting his legs let him know that both legs were also cuffed to the railing of the bed.

“I see you’re awake.” The voice sounded darkly amused and Dean winced at the sound, groaning again and turning to stare at bright red lips curled in amusement. “We’ve kept you sleep for quite awhile so you could recover from your injuries and your surgeries.”

 _Surgeries?_ Dean wondered mentally as he finally placed the woman standing next to the bed. _Abaddon_. She was one of Lucifer’s enforces and a vicious alpha who was widely known for the amount of torture she inflicted on her victims before finally ending their lives.

She was even more well known for the way she left omegas after they had graced her bed.

“There was quite a bit of tearing around your anus and throat where it was forced open, evidence of repeated violation and cuts littering your body among other types of internal damage.” She gave a look of mocking sympathy, “You poor thing. You’re healing quite nicely and you’ll survive.”

“What do you mean by surgeries?” he croaked, swallowing and coughing, as something wicked appeared in Abaddon’s cold eyes and dread filled him.

Her lips quirked and she made a show of looking at a clipboard. “Surgeries. Hmmmm…oh yes. You were chipped so we could keep track of you and to make sure you don’t leave the boundary of the room you’re placed in at Lucifer’s property once it’s been activated. And since you are to be placed at The Cage to pay off what you owe Lucifer we took the liberty of removing your balls and reducing your dick while you were unconscious.” A low laugh escaped as horror had Dean’s face twisting, “You won’t be needing them since you’re for Lucifer’s more deviant alpha clients who enjoy fucking and knotting other alphas. And a big alpha dick would just be...unseemly for your new position. You're now at a little over an inch long, your knot removed, so you're closer to an omega's size and far more attractive to alphas wanting to use you.”

“ _No_.” Dean whispered. He had hoped he’d imagined Alastair’s words or that the whole thing had been a nightmare. “ _No no no no_.”

She only laughed in pure amusement and let her eyes rove over him. “Yes.” Abaddon enthused, “And Lucifer’s doctor has cleared you for work. You’ll start the second you’re placed in your new room and I already know there are quite a few of Lucifer’s clients who are excited to help break in the new alpha whore at The Cage.”

“You won’t be able to keep me there.” He swore, desperately clinging to the thought of escape and eventually saving Sam. Dean couldn’t believe this was it.

The words only earned him a tsking sound, “That’s what the chip is for, _Dean_. Not only does it keep track of you but it is placed so that if you cross your room’s boundary it will paralyze you and only when Lucifer deactivates that feature will you be able to move again.” She patted him, “And that’s if you can remove the chain you’ll be fitted with once you get there. We haven’t had any alpha at The Cage escape.”

“Then I’ll kill myself.”

“If you do that, not to say that you’ll succeed, then Lucifer will take it out on your precious little Sammy.” She leaned close, “And Alastair very recently acquired two pretty little acquaintances of yours who will suffer for it as well.”

Dean tried desperately to think of who Alastair could have possibly gotten ahold of but his mind was scrambling to make sense of everything. From the creature, to his repeated rape, birthing an unknown number of creatures and waking to yet another nightmare it was hard to get his brain to work fast enough to keep up.

The horror of the situation was beyond anything he could begin to comprehend at the moment.

“Who?” he demanded hoarsely.

“I believe the Novak twins, Jimmy and Castiel, are _friends_ of yours?” Abaddon stroked his cheek in a mocking gesture as Dean jerked away and snarled at her, “Two pretty little omegas I believe you had thought about choosing one to mate, had you not?”

He had.

Dean had been waiting until they had turned eighteen before he wanted to claim one as his own but they had only recently turned seventeen and they were closer to Sam’s age than his own so he had been a bit more hesitant not wanting to take advantage.

“Alastair wanted me to tell you how good they both felt when he had fucked and knotted their little cunts.” Her fingers tangled in his hair and yanked so they locked eyes, “How they had cried and begged him to stop before he tied them down to be used by _all_ of Lucifer’s alphas. Both of them have been _fucked_ by well over a hundred times last I heard.”

Tears burned his eyes at hearing what had happened to the Novak twins and knowing Lucifer had Sam. He felt helpless as Abaddon forced him to listen to every single word about the Novak twins and Sam.

“I made sure to take a turn with both of them myself. Fucked their little cunts raw until they were sobbing and begging me so deliciously.” Her eyes hooded, “You should have seen the way their little flat bellies had swelled with all of that Alpha come pumped into their cunts.”

He had failed. Dean was so lost to the mental pain and anguish that he didn’t notice the nurse come into the room to inject him with a sedative. His focus on the world slipped away as he dropped right back into unconsciousness.

* * *

A hard smack had him jerking awake with a muffled moan.

The room was barely lit as he tried to figure out where he was but Dean didn’t recognize anything. He shifted, planning to sit up from where he was laid out on his stomach, but restraints kept him in place and had his breathing quickening.

“Finally.” The voice had him twisting and failing to free himself, “I’ve been waiting for you to wake up so I could enjoy my reward. Lucifer is a very generous employer and I want to get everything out of this.”

Alastair squatted in front of him, completely naked, as Dean tried to respond only to realize a ball-gag had been shoved into his mouth. Everything slammed into him all that once, the horror and fear and realization, as he stared into Alastair’s alpha red eyes.

“I didn’t want to deal with the pathetic threats but it won’t stop the sound of whimpers and sobs when we really get going.” Alastair rose to his feet and Dean could catch the scent of Castiel and Jimmy on the alpha before him. It had rage twisting inside of him as Abaddon’s words from before taunted him. “I’m going to enjoy being your very first alpha dick and knot even if I won't be the first in that tight alpha hole of yours.”

Wet fingers prodded against his hole, pushing inside and pumping, as Dean jerked and snarled against his gag at the unwanted touch. He could smell alpha arousal thick in the air and it had his instincts rebelling violently against the touch of another alpha.

The need to fight against the forced submission to another alpha had him clenching down and fighting even harder against his restraints but he had been thoroughly secured.

“Just enough slick to ease the way.” Alastair breathed out, “I even thought to bring actual omega slick to fuck you with. I’m sure you can smell it. It’s from little Cas. Gave him a shot to force him into a false heat, gathered up some slick and then let some of Lucifer’s alphas enjoy themselves. He was moaning like the pretty omega whore he was born to be and taking a nice, thick and long alpha dick in his dripping cunt when I left to come here.”

More of the slick, _Cas’s slick_ , was added to his dry hole before Alastair seemed pleased enough.

“But don’t worry. His equally pretty twin isn’t empty for long but I had lent him out to Abaddon for the weekend. She does love making omegas scream and beg, doesn't she?”

That was when Dean felt the blunt head of a thick, unwanted alpha cock pushing against his resisting hole. It forced its way inside, splitting him open and making Dean think of a hot poker being shoved up into him, as Alastair thrust forward until he was completely buried inside. The pain was undeniable and he felt tears spilling, unwanted, down his cheeks.

“I’m not one for fucking another alpha but for you I’ll have to make an exception every once in awhile. I do _love_ seeing you in pain, Winchester.”

Fingers gripped his hips and without waiting for Dean to adjust Alastair started to rapidly fuck into him. Dean howled against his gag and tried to shy away as humiliation at being in such a position filled him completely.

“Tight.” The word was snarled as the thrusts came harder and faster and far more vicious then they had any right. “Lucifer is going to make a mint on your ass and those cocksucking lips.”

Dean’s ass clenched tightly and his fingers curled as pain raced through him. Over the roaring in his ears he could hear Alastair’s grunts of pleasure, the slap of skin against skin and his own whimpers filling the darkened room as the first of what promised to be many alphas fucked him in the dark room he’d woken up in.F

**Author's Note:**

> Prompter wanted these points included:  
> -Mobster Alpha Lucifer punishing Dean for trying to send away little Omega Sam  
> -Alastair as an Alpha enforcer who hates Dean  
> -Alpha Dean fucked repeatedly by tentacle monster  
> -Dean forced to repeatedly incubate monster's offspring and birth them (with lots of pain)  
> -Dean castrated and chipped so he can't escape  
> -Alpha Dean forced into prostitution at one of Mobster Lucifer's clubs  
> -Dean a much older brother to Sam/still highly protective (Dean in his twenties and Sam in his teens)  
> -Dean threatened with Sam and Omega Novak twins  
> -Include Mobster Alpha Lucifer/Young Omega Sam with little Sam getting punished  
> -Also Alpha Alastair/Young Omega Cas/Young Omega Jimmy (with some kind of gangbang Dean can be taunted with).  
> -LOTS OF HURT/ABUSED DEAN (physical/emotional/etc)
> 
> As always I hope someone enjoyed my latest posting. It's very dark, has a variety of kinks and it just as fucked up as any of the other prompt fills I've posted before. Thanks for giving it a shot!
> 
> Note: In case anyone was curious I created a tumblr account at [thursdayhunter](http://www.thursdayhunter.tumblr.com) for communication outside of the AMAZING comments you all leave for me on my fics. It's one way I've received prompts or at least ideas for some of my fics on here. I do consider prompts sent to me or if someone has found a prompt on the kink-meme they think might be up my alley.


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